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By Jeremy CaplanTechnologyEducationHow To
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Wonder Tools episodes

  • How I’m Using AI Agents 👁️‍🗨️

    I’ve never had a secretary before. Or a chief of staff.

    With these AI agents, I suddenly feel like I have both.

    This week, among other things, they:

    * Researched and booked Amtrak train tickets for me

    * Briefed me about important overnight emails and upcoming meetings

    * Surfaced an important contract I had overlooked

    * Turned my bookshelf into a visual reading list

    Unlike older chatbots, these agents can take action proactively without waiting for a prompt. They can go online and research or buy things, make reservations, or fill in forms. They can look through various documents, transcripts, and emails to help you finish tedious projects.

    I’m testing 12 agents

    Agents are the biggest step forward for AI this year. I’m testing a dozen to compare their reliability, features, and design: Thine, Instinct, ChatGPT’s Dots, Town, Hark, Muse, Poke, Ambi, Sentience, Extra, Slashy, and Claude’s Duet.

    My early favorites: Dots, Slashy, and Hark

    * Dots has helped me spot calendar conflicts and find and prepare materials I need for work. I use it several times a day.

    * Slashy has changed how I manage email. It’s a strong alternative to Superhuman, the email app I’ve used for years. Slashy puts an AI agent inside my inbox.

    * Hark has a standout design. It’s been reliable for shopping and reservations.

    Other observations

    * Business agents will be a separate category. Town, for example, is easy to use and well-designed, but its features are tuned to small businesses and mid-market firms.

    * These are early impressions. I’ll share more as the tools develop. I’m working on a post about Slashy and how to use AI to help with email overload. The inbox is where I see early agents being most helpful.

    One is enough

    Start with one agent that does what you need. I’m testing a bunch for now, but ultimately I’ll prioritize just a few with distinct strengths.

    What they cost

    Some agents, like Instinct, Hark, and Muse, start out free. Others require a paid subscription.

    * Dots is so far only available on ChatGPT’s Pro plan, which starts at $100/month.

    * Town starts free, but the Pro plan is $49/month.

    * Hark starts free. Upgrade for $20/month for more AI usage or $100/month for full power.

    * Thine is free to start. It’s $15/month or $120/year for extra capabilities.

    * Pricing for other agents is still taking shape. You can test many for free. Before connecting your accounts, check on ongoing costs and how each service uses your data.

    Connect your email, calendar, and files

    Thine and Dots became much more useful as soon as I connected them to my email, calendar, documents, and Granola meeting transcripts. Now they have a broad view of my projects for context, as well as a detailed understanding of my emails and tasks. Drawing on meeting transcripts, they even understand what I’ve promised to do.

    2 reasons to try an AI agent

    * They save time by handling pesky tasks that used to take hours. Examples:

    * Hark coordinated a tricky travel itinerary and handled the booking on Amtrak’s clunky site.

    * Dots pulled a batch of related emails into a doc, a task that would otherwise have taken me 45 minutes.

    * They prevent headaches. They don’t wait for me to send a prompt. Numerous times they’ve helped me avoid costly errors. Examples:

    * Dots found an appointment mentioned in a buried email and alerted me that it was missing from my calendar.

    * Thine reminded me to send an important email I had forgotten.

    5 differences between agents and chatbots

    * They’re easier to get started with. Claude Code, Codex, and tools like Hermes Agent are at least as powerful as most agents I’m describing here, but they can seem intimidating. Setting them up is a bit like learning to use a manual camera. You have to figure out which connections to enable, which plugins to add, and which skills to install. Agents like Thine, Hark, and Town are more like point-and-shoot cameras. They guide you through setup and connections to your calendar, email, Notion, etc., with explanations in plain language.

    * You text them like a person. Many agents, like Instinct, Poke, and Slashy, work in SMS, iMessage, or WhatsApp. So you don’t have to open an app or browser tab. It’s like messaging a colleague instead of walking over to the help desk.

    * They reach out to you. Chatbots wait for your prompt. You might go days without remembering to use one. Agents send morning briefings, flag missing details on your calendar, and nudge you about unsent drafts. It’s the difference between a chief of staff who knocks on your door versus a reference librarian waiting at a desk.

    * Flexible models. Most agents can switch among models from different AI providers, like travel agents who can book any airline. ChatGPT, Gemini, or Claude rely primarily on their own models.

    * You have one ongoing conversation, not hundreds of chats. I like how Thine and Dots keep a single long-running thread. Both remember our past conversations reliably. Chatbots I use scatter my history across lots of threads, which can make older exchanges hard to find.

    The lines are blurring

    For now the differences are noticeable, but major AI companies are adding similar capabilities. OpenAI’s Dots is already an excellent, if expensive, agent, and Claude Duet arrived on October 23.

    I avoided the first generation of AI agents, like OpenClaw, because they seemed complex and risky. But several agents I’m testing are easy to use, and free to try.

    What I hand off, and what I don’t

    My goal isn’t to outsource my thinking or writing. I enjoy both. I want agents to handle background tasks like filing, organizing, and checking email for important messages. Or filling in annoying online forms. That leaves me more time to concentrate, with less worry that I might be missing an important message or task.

    4 ways my AI chief of staff helps

    1. Tame my inbox

    I now get three times as many emails as I did three years ago. Many are AI-generated marketing or PR messages. With that email slop strewn across my three addresses, it’s easy to miss an important message among more than 1,000 emails a week. AI agents help me:

    * Summarize important new messages. At 8 a.m. my agents text me a summary of important emails from the previous evening and overnight. Instead of starting the day by scanning through hundreds of messages, I can just act on five important ones.

    * Handle irrelevant email for me. I respond myself to important and personal messages. But I don’t have the four hours it would take to reply to the hundreds of unsolicited, irrelevant emails I get every day. My agent can sort and archive those, or, in some cases, suggest quick “no, thank you” notes I can edit.

    2. Plan my day

    Mapping out my day at 8:30 a.m. means fewer decisions later, when I’m less focused, about what I should be doing.

    My agents can look at my calendar, email, project materials, task list, and notes to suggest a detailed plan based on my preferences. They know I need breaks for stretching and meditation, a lunchtime walk, and time to call Mom. They use data from Rize, my time-tracking app, to estimate how long tasks usually take me.

    During my Friday review, they help me reflect on next week’s priorities, tasks that need follow-up, and long-term projects to start. I head into the weekend feeling less stressed.

    3. Research tricky decisions

    In a day, I might have five to 10 questions an AI butler can help me research. I recently needed to turn 11 lengthy Google Docs into a printed book. I had to compare file conversion tools, check prices and reviews for book-printing services, and understand the technical steps.

    That research would once have taken me an hour or more. This time I asked an agent to handle it and went back to preparing to teach. About five minutes later, my agent delivered an excellent recommendation in the Google Doc I’d requested.

    I don’t like shopping. But I like knowing I’m getting a well-reviewed product or service at a good price. Hark and Instinct can compare options, recommend what to buy, and set up the purchase for me to confi…



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    17 min
  • 5 Writing Tools to Get Unstuck ✍️

    The hardest part of writing is the first 10 minutes. Get past that, and momentum kicks in.

    Once you start scribbling a few sentences, you’re on your way.

    Having gotten stuck and unstuck a lot over the past 325 weeks of writing this newsletter, I’ve found a few tricks that help. Pick one to try, and leave a comment to share what you do to get unstuck.

    As a little experiment, I’ve made an Unstuck Studio page to accompany this post and to help you get unstuck playfully.

    As Daniel Pink explains, starting comes first.

    “Action precedes motivation, not the other way around.”

    When I’m stuck, I dictate rather than battle my inner critic.

    The critic assumes there’s a better word for whatever I’m typing. It urges my fingers to stop and wait. When I’m rambling with my voice, the critic is quiet.

    We call an idea freeze writer’s block, not talker’s block. When we speak informally, ideas just flow. Because spoken words disappear into air, it’s easier to avoid self-editing. In a dictated draft, clunky first words are OK because they get us closer to what we’re trying to convey.

    Tools I use for dictating first drafts

    * Google Docs voice typing works in more than 100 languages. In English you can add punctuation verbally or say things like “new paragraph.” See more of my favorite Google Docs tips and tricks. Free.

    * Letterly works well on mobile or desktop. In addition to transcribing, it can give you a summary, or format your text. (It’s now a free perk for paid Wonder Tools subscribers.) Free with limits, or $80/year.

    * Wispr Flow lets me dictate into any app or site on my laptop or phone. It works surprisingly well even if I whisper, which helps around other people. I just double-tap my Mac function key and start talking. Free to start; $12/month for pro features.

    * Lispr.ai is a reliable Mac option. It can also translate your dictation. Free.

    Simple alternatives: iOS Voice Memos and Notes transcribe your speech for free. On Android, try Google Keep.

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    The Most Dangerous Writing App erases your words if you stop typing before your timer ends. Choose a three or five minute sprint, or set a word target. Once you get the hang of it, your hands will keep moving. Edit later. Free

    Ilys is an even more challenging way to force yourself to keep writing. It shows your typing just one letter at a time. When your session is over, you can review and edit your words.

    Free for basic use. Sessions are capped at 808 words, which is more than enough for freewriting. A subscription is $11/month, but I don’t need the extras.

    Mind maps help you focus on concepts and ideas, rather than piling words onto the page. Connect your ideas to one another visually. Put one word down. Add a picture if you want. Pretty soon you have an outline to build on.

    When I’m writing something complex or juggling lots of ideas, mind mapping allows me to assemble the bones of a piece efficiently. Use Apple’s free Freeform app on iOS or Mac. Or try simple apps like Mindmup or Bubbl.us. Both are free for up to three maps. Miro and Mural, which offer more advanced design features, also give you three free boards.

    Rather than using AI to write, ask it to interview you. Or push it to provoke you. I find that helps me surface my own thoughts.

    Prompts to try

    * “Interview me about this. Ask one question at a time. Push me for depth.”

    * “Provoke me. Give me a controversial statement to respond to.”

    * “Push me to sharpen my viewpoint by pointing out potential blind spots in the ideas I’m starting to write about.”

    * “Ask me five intriguing questions about this. Don’t answer any of them.”

    * “Act as a tough mentor. Give me five unconventional writing prompts to pick from ….”

    * “Ask a surprising question I’ve not heard before …. Include a feasible writing target to complete in the next 10 minutes.”

    This last tactic is tech-free.

    * Grab a piece of blank paper.

    * Fold it in half three times. You now have 8 rectangles.

    * Challenge yourself to put one sentence or phrase into each of the boxes. Set a timer to repeat every minute. Move to the next box each time it rings. Eight minutes later, you have a bunch of sentences to build on.

    Slogans tell us that discipline propels people toward accomplishments. That sounds logical. But when I’m staring at a cursor, discipline alone doesn’t clear the fog. These tactics do. What helps you get unstuck? Leave a comment. 👇

    More writing tool recommendations



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    7 min
  • The Newsletters I Read First

    I subscribe to hundreds of newsletters. Most weeks I read only a fraction. These are the dozen free ones I turn to first, all written by humans, plus five bonus picks from two guests. Share your favorites as a comment below.

    1. Dense Discovery by Kai Brach

    The best curated email I get. I find interesting sites, stories, and ideas in each post. It’s also gorgeously designed. It has a 63% open rate, roughly double the typical newsletter. For a sample, check out the recent “Cynicism is not a strategy” issue.

    2. NextDraft by Dave Pell

    I abhor the frenzy of 24-hour news cycles. But it’s a pleasure reading Pell’s daily NextDraft. He summarizes the day’s most interesting stories with a warm sense of humor, avoiding the anxiety-provoking tone of nightly TV news. He always includes at least one offbeat story that’s fun to share. WTF Just Happened Today also serves up a clear, concise take on today’s top U.S. news.

    3. Cool Tools by JR Raphael

    I always learn something from Raphael’s posts. Instead of chasing tech headlines, he tests and explains useful sites and services. His separate Android Intelligence email catches me up on new apps outside the Apple world.

    I also like Recomendo. The three contributors spotlight six useful things in each issue, from a fantastic site, book, or video to an unusual hardware tool or a helpful Reddit community.

    4. One Useful Thing by Ethan Mollick

    The most insightful AI newsletter I read. Mollick, a Wharton professor, shares practical AI experiments with his 480,000 subscribers, testing what the tools can and can’t do well. Every few months he writes an opinionated guide, like this guide to which AI platforms you should try. His latest post features an elaborate music video he had Claude compose with Suno. His book Co-Intelligence, published in April 2024, remains a helpful AI primer. I’m looking forward to his next book, Co-Existence, coming out October 20.

    5. Hulry by Rahul Chowdhury

    Chowdhury blends common sense with creativity. His recent post, 21 Productivity Hacks I’ve Picked Up Over the Years, is a good example of his straightforward, practical takes. Like Dense Discovery, his Hulry posts are full of well-chosen finds. Each issue has something handy or quirky that’s fun to read about.

    Sponsored Message

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    6. Popular Information by Judd Legum

    The best example of an independent investigative journalist making the Substack model work. It’s completely free to read, supported by paid subscribers, with no ads. Legum aptly describes his project as “News for people who give a damn.”

    His accountability scoops on corruption and injustice lead to change. They’re full of carefully reported details and regularly picked up by major news outlets. One example of his impact: in 2020, after his reporting about Olive Garden, its parent company started providing paid sick leave to about 170,000 employees across 1,779 restaurants.

    7. Second Rough Draft by Richard J. Tofel

    Read this excellent newsletter if you’re interested in the state of contemporary journalism. Having been ProPublica’s first employee and its president from 2013 until 2021, Tofel brings experience, expertise, and evidence to his posts. He’s warned that many of the nation’s for-profit metro newspapers are “going out of business in slow motion.” His posts show how and why that’s happening, while also offering insight into the nonprofit news world.

    8. Dr Phil’s Newsletter by Dr Philippa Hardman

    Not that Dr. Phil. Hardman, a Cambridge University scholar, shares research-backed insights about how AI affects learning and teaching. Posts feature clear charts, frameworks, and novel ideas about AI and education. One recent writeup I appreciated explored the research on whether AI-generated videos actually help people learn.

    9. The Pink Report by Daniel Pink

    I’ve never met Pink, but I learn from him every week. His weekly pieces work as brief classes in wisdom, like 30 cheat codes for life and six skills humans need in the AI era. I especially enjoy Pink’s reading recommendations, like 11 essential books for 2026 summarized in 12 minutes. He’s as skillful at writing hundreds of pages as he is at drafting short videos. His book When explores the best times to do things. Watch his YouTube videos for short versions of his advice.

    10. 3-2-1 by James Clear

    I like Clear’s brevity. Three short ideas, two quotes, and one question to ponder. The formula has worked well enough to attract 3 million subscribers, more than any other publication on this list. I wish he’d write another book, given how good Atomic Habits was.

    11. Techmeme

    I check Techmeme daily to keep up with tech news. Its headlines sum up what’s new with AI and tech and link to multiple takes on top stories. There are many tech portals and aggregators, but this one has remained in my rotation year after year.

    Two newer alternatives: Set up custom scheduled reports with Claude or ChatGPT. List your favorite topics, angles or outlets to highlight/avoid, and how often you want it. If you prefer manual curation, use Mailbrew to assemble your own digest. (Read my take).

    12. Nice News

    When I feel worn down by the news, I turn to this sweeter space. It’s full of hopeful pieces, but not random raccoon GIFs. One recent piece celebrated medical research breakthroughs, while another was titled “‘16,648 Reasons to Live’: Paper Highlights the Power of Small Joys for Suicide Prevention.”

    To add to my recommendation list, I invited James Potter to share two of his favorite newsletters. He runs Reletter, which tracks around 7 million newsletters across Substack, Beehiiv, LinkedIn, Ghost, and more.

    Potter recently mapped how newsletters cluster based on the links they share (reletter.com/graph). He publishes a weekly ranking of the most-cited links. It’s a superb resource for keeping tabs on what people link to most.

    13. Stratechery by Ben Thompson

    James: I’ve paid for Stratechery since 2021. If I could only keep one newsletter it would be this one. Thompson writes about the business strategy behind tech news. Whenever something happens, he works out who ends up with power over whom. His main tool is a framework he calls Aggregation Theory, which says that whoever owns the relationship with users gets leverage over everyone supplying them. He’s great at weaving his past analysis into current issues and tying everything together.Recently he wrote an interesting article about the idea of AI agents doing your shopping for you. Walmart was one of the first big retailers to sign up for OpenAI’s Instant Checkout. Walmart pulled out a few months later because orders placed through ChatGPT converted at a third of the rate of its own site and app, and the baskets were smaller too.

    14. Benedict Evans

    I read Evans’s email every week. It’s how I catch up on anything in tech that I missed. I also like his way of seeing the world. He spent years as an analyst and was a partner at Andreessen Horowitz. Each week he picks the tech stories that mattered and adds a few lines of context to each, often with a dry joke. He’s good at checking hype against the numbers.

    When SpaceX filed to go public, for example, Evans wrote about how xAI’s data center provides services to Anthropic for $15 billion a year, more than SpaceX’s entire launch business.

    ❤️ What newsletter do you like? Leave a comment ↙️

    Jeremy: To close, I asked Julia Sherwin to share her favorite newsletters. Julia is an assistant publisher at GlobalPost Media. She’s also executive director of the GlobalPost in the Classroom, a program that offers free subscriptions to faculty and students at high schools and universities worldwide.

    I asked for Julia’s take because I love GlobalPost. It’s great for discovering interesting issues in countries …



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    10 min
  • 🔕 Too Distracted? Try These Tools

    Now that fall is here, my focus has been fragile.

    Noise, notifications, news, and email grab at my attention.

    To help cope with distractions, I've stitched together a focus toolkit with apps, sites, and sounds. Some are new, others old. My goal this season is to concentrate for a bit longer when my attention might otherwise drift. I hope this collection will be useful for you too.

    Stop email interruptions 📧

    Inbox Pause

    This simple email add-on temporarily freezes what you see in your inbox. Any new messages will show up as soon as you un-pause.

    Price and platforms: Free for basic use. For extra features, like custom scheduling or hearing from select senders during pauses, get the $15/month pro account. Works with Gmail and Outlook online or on the iPhone. An alternative free option: Pause Gmail

    Avoid distracting sites 💻

    News Feed Eradicator

    Get rid of the addictive endless feed on social media sites like Facebook, Twitter, Reddit, YouTube, and LinkedIn. Look instead at whatever accounts you’re actually interested in.

    Price and platforms: Free. Chrome only.

    Raycast Focus Mode

    Block email and distractions during short, focused, work sprints.

    Price and platforms: Free. It can automatically block sites for you in Safari, Chrome, and Firefox (and related browsers modeled on WebKit, Chromium, and Firefox).

    SelfControl ⏳

    Pick a list of sites to block. Set a timer for deep work. While it’s active, you won’t be able to use Facebook, email, or whatever you’ve blacklisted, even if you restart your computer.

    Price and platforms: SelfControl is free for Mac. It’s open-source and not fancy.

    Alternative: Cold Turkey is a more polished free Windows and Mac alternative for blocking sites. The pro version costs $45 for a lifetime license ($36 for students) for advanced features like blocking applications.

    Forest App

    Rather than blocking sites or apps, Forest helps you avoid wasting time on your phone by rewarding you for not touching it. Your virtual trees grow until you pick up your phone. The approach seems to resonate: 60 million people have used this app. 🌳

    Price and platforms: Free for iOS and Android. A paid subscription unlocks extra features.

    Apple Screen Time

    Set time limits on apps that tempt you to doomscroll. Count how many notifications your apps send, and see how much screen time you’re logging. The downtime feature is what I use most. It closes my apps at 11pm. I can override that when I need to. But I like that friction nudging me to stop late-night work.

    Price and platforms: Free for Macs and iOS devices. Android has a related “Digital Wellbeing” feature. And Windows has focus options. There’s a related Do Not Disturb mode for Mac and iPhone.

    Wonder Tools Quick Survey

    Help me understand who reads Wonder Tools and what matters to you. It takes about a minute. As a thank you, you’ll get my updated list of 100+ favorite tools in an email within days of submitting it. Your responses are confidential.

    Block noise 🔊

    Sony Noise Cancelling Headphones

    The New York City subway is painfully loud. So I splurged on these over-the-ear WH-1000XM6 headphones. (My previous XM3 pair lasted for seven years until I accidentally bent them.) The battery lasts for several weeks on a single charge.

    Price: $460. The XM5 model, also excellent, is $300. Wirecutter’s review (which agrees that Sony’s XM6 model is the best) includes a $100 alternative.

    MyNoise

    Pick your favorite type of focus sound: a waterfall, a purring cat, white noise, rain, or a dozen others. I like the cafe, where you can adjust the ratio of chatter to kitchen noise. The creator, Stéphane, records real sounds and wrote a manifesto about avoiding AI-generated noise. The newest release: Pigeons of NYC.

    Price and platforms: Free, browser-based.

    Headspace

    This was designed as a meditation app, but I use the focus music without lyrics to block noise around my Times Square office.

    Price: $70/year or $10/year for students. Or share six accounts (family, roommates, teammates, etc.) for $100.

    A Soft Murmur

    Mix a range of sounds to block out city noise or whatever annoys you. Customize and save your own sound mix. Here’s my blend of waves, wind, and white noise.

    Price and platforms: Free, browser-based.

    Give your body a break 🧍

    Wakeout

    Take quick exercise breaks with short video loops showing real people doing cardio moves. I like one-minute exercises. The newest version adds little movement games. Body breaks improve my focus.

    You can also use Wakeout to pick apps that pause when you’ve been sitting too long. Moving brings back access. (Manoush Zomorodi’s new Body Electric book makes an excellent case for the value of quick movement breaks.)

    Price and platforms: The Chrome browser extension is free; a subscription for iPhone, iPad, Mac, and Apple Watch is $70/year or $13/month.

    Time Out

    Rest your eyes periodically if you work at a screen. I set Time Out to remind me to give my eyes a screen break every 15 minutes. You can choose your own interval. It nudges me to look out the window and stretch. It’s an old app, but it still works.

    Price and platforms: Free, optional contributions of $5 to $60. Mac only.

    Alternatives: BreakTimer is simple, free, and works on Mac, Windows, and Linux. Restier is a little more polished and also works across platforms; $9 for one device or $15 for two. Lookaway is an elegant Mac option that starts at $19.

    Nex Playground

    I spend most weekdays standing in front of my computer, so I love how the Nex gets me moving. Its 60+ motion-sensing games are played with your body, not thumbs or controllers. My daughters, wife and I have it linked to our New York City apartment TV and I appreciate how it boosts my energy for evening work. It’s also great for short breaks that reset my focus when I work from home.

    Price: $300, plus an optional $89/year subscription for all 60+ games

    Hold yourself accountable 🤝

    Focusmate

    Pair up with an accountability partner online. Pick a time on the site’s calendar when you want to get work done. Choose an interval of 25, 50, or 75 minutes. You’ll be paired with a real person who also wants to stay focused. Log in at the appointed time.

    I was originally skeptical about this “body doubling” tactic. I found, though, that an appointment with another human made it feel like a special work interval. It did feel a bit silly to have to meet a random person over Zoom to trick myself into concentrating. But if that’s what works, I’ll do it on occasion.

    Price and platforms: No app or download required. Works on any computer or mobile device with a camera and microphone. Free for up to three sessions a week, or $8/month billed annually for unlimited.

    Stickk

    Pick a goal and create your own commitment contract. You can pledge to donate to a cause you don’t support if you fail to follow through on your resolution.

    Price and platforms: Web-based. No cost beyond what you decide to commit.

    BeeMinder

    Make commitments tied to data you sync. Works with categories like time spent on Facebook or whatever else you choose to sync from Toggl, Fitbit, or other time or health-tracking platforms. Here’s a video explainer.

    Price and platforms: Web-based. Free or $8/month for extra features.

    Learn new strategies 📚

    Tranquility by Tuesday

    My favorite book by Laura Vanderkam offers nine ways to make time for what matters. I like her suggestion about carving out a time slot toward the end of each week expressly for finishing things you’ve fallen behind on. I enjoyed talking with her about her latest book, and you can read more of her tips in her Vanderhacks Substack.

    Deep Work

    Cal Newport is a computer science professor and New Yorker writer who argues that computers and other devices can ruin our focus if we don’t use them thoughtfully. I found it helpful in exploring how to separate technical and menial tasks from work that requires slow, non-linear thinking.

    Indistractable

    Nir Eyal stuffed his excellent guide to staying focused with useful insights. It’s full of research-backed ideas for combatting internal and external distra…



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    13 min
  • 🧠 How to Improve Your AI Skills

    Today I’m sharing a guest post on how to strengthen your AI skills. It’s by Frank Andrade, an AI instructor who has helped thousands of people on Substack master ChatGPT and Claude with beginner-friendly guides and in-depth tutorials.

    Frank: The gap between AI novices and experts is growing.

    * One group is saving 5 minutes on emails.

    * Others are running systems that work while they sleep.

    The good news? You can progress faster than you might think.

    The Five Stages:

    * Stage 1: AI Beginner

    * Stage 2: Prompt Crafter ⬅️ (where many people stall)

    * Stage 3: AI Literate

    * Stage 4: Workflow Builder

    * Stage 5: System Builder

    Regardless of which stage you’re at, the resources in each section below will help you sharpen your AI skills.

    Stage 1: AI Beginner

    This is where everyone starts.

    You have a ChatGPT, Gemini, or Claude account. You use it like a fancier Google. You ask one-off questions. Maybe you ask it to help write a quick email or generate a few images. That’s about it.

    It’s useful, but it doesn’t feel like a superpower yet. Don’t worry. We’ll get there.

    The first move at this stage is picking your tools.

    AI tools fall into two categories:

    * General-purpose: Handle multiple tasks including text and visuals

    * Task-specific: Focus on a specific kind of content or media type

    Frank’s Recommended Toolkit

    Start Here

    Claude, ChatGPT and Gemini

    Worth Exploring

    Gemini Notebook, Claude Cowork, and Claude Code

    Specialized Tools

    Gamma (presentations), Google’s Nano Banana Pro (images), ElevenLabs (audio), HeyGen (video), and Napkin (infographics)

    The Big 3: Select a Starting Point

    For beginners, the differences between ChatGPT, Gemini, and Claude aren’t significant. Still, here are some things to keep in mind:

    * ChatGPT: rich feature set, including voice and video modes and image generation

    * Gemini: works well with Google Docs, Sheets, Gmail, YouTube, etc.

    * Claude: strong at automation and building tools/apps; doesn’t generate photos or videos, though it does assist with design

    If you’re a beginner, pick one to focus on. It’s fine to select what your company provides, what’s familiar, or one you’re curious about. Stick with it for a few weeks to see when it saves you time, how well it handles technical tasks, and where it’s most useful.

    Frank’s current stack: Claude Cowork, and Claude Code for serious work, Gemini Notebook for learning, and ChatGPT for voice.

    Your stack doesn’t have to look like mine. Build your own based on what you actually do.

    Here are some of my resources for this exploratory stage:

    * The Best AI Tools for 2026

    * Your Guide to ChatGPT

    * Claude for Beginners: Complete Guide

    Stage 2: Prompt Crafter

    When it comes to AI chatbots, how you ask is as important as what you ask.

    At this stage, get to know this basic prompt structure:

    * Instruction: what you want

    * Context: background the AI needs to know

    * Constraints: length, tone, format, things to avoid

    * Example: when possible, provide an example of what “good” looks like

    For more detail, refer to this robust prompt formula shared by Anthropic, which makes Claude:

    You’ll rarely need to use all the elements of the formula, but it’s good to know they exist. Think of them as a menu to pick from.

    At this stage, you should also know a few prompt-improvement tricks. For example, when you finally land on a great answer after a long back-and-forth, ask the AI to write the prompt that would have gotten you there on the first try.

    Here are some resources for this stage:

    * Prompt Formula

    * Prompt Principles

    Who Needs to Go Beyond Stage 2?

    Stage 2 was enough in 2023.

    In 2026, AI has evolved and can run multiple tasks at once on its own. There’s nothing wrong with being in stage 1 or 2 if you’re a casual user who proofreads emails and generates images once in a while

    But if you want to master AI, you need more.

    That’s what we’ll cover in the next stages:

    * Stage 3: Develop AI literacy. Use it as a thinking partner.

    * Stage 4: Build AI workflows for the work you do repeatedly.

    * Stage 5: Build AI systems that run while you sleep.

    Stages 3, 4, and 5 are for professionals, builders, and business leaders who want to turn AI into a competitive advantage.

    Stage 3: AI Literate

    Understanding how AI actually works changes how you use it.

    People with AI fluency know when to trust AI outputs, when to push back, and how to frame problems to get more useful results. That’s what separates those who use AI as a novelty from those who deploy it for its practical advantages.

    People at this level know these AI concepts:

    * Hallucinations: AI can confidently fabricate facts, stats, and citations. Always verify outputs when accuracy matters.

    * Context Window: AI assistants can remember a limited amount per conversation. Once that limit is exceeded, your AI forgets earlier context.

    * AI Sycophancy: AI models are trained to be helpful, sometimes to a fault. They may validate your perspective even when you’re wrong. They rarely challenge assumptions unless prompted.

    * Knowledge Cutoff Dates: Models generally have training cutoffs. That means they may not know about recent events. If an AI assistant has access to web search, it can gather new info.

    * Data Bias: AI inherits biases from training data. Be cautious when using AI for decisions about sensitive topics.

    * Privacy & Safety Basics: Know the data policies for your AI tool and your organization. Read about how to use private AI tools for free, and how to set up a private AI toolkit.

    Having AI literacy means knowing how to manage AI limitations.

    Example: Let’s say you’re a leader who wants to combat AI sycophancy to make better decisions. Create anti-sycophancy instructions that nudge an AI assistant to disagree with you constructively.

    At this stage, move from “AI thinks for me” to “AI helps me think better.”

    That means using AI as a sparring partner. Here are some ways to do that:

    Ask AI to generate different solutions and grade them

    “Generate three solutions. Score them from 1 to 10 and justify the score.”

    Use AI to critique responses, opinions, plans, etc.

    “Be my adversarial friend. Argue the strongest case against Option A. List five reasons why it might fail and the early warning signs. Suggest five ways to reduce those risks.”

    Generate questions to refine outputs

    “Before drafting anything, ask the five questions that would most alter the outcome of this memo: [1-sentence purpose].”

    Resources for this stage:

    * How to use AI as a thinking partner

    * Before your next big decision, build this Claude skill

    * Books to increase your AI literacy

    * How to build your AI Mentor

    Stage 4: Workflow Builder

    The trick at this stage is designing your own workflows, not using more tools.

    A workflow is a multi-step process where AI plays a role at each step. You might still drive it by clicking, uploading, and reviewing. But you don’t start from scratch every time.

    Here’s a workflow I built:

    Learn a foreign language with AI

    * Step 1: I answer questions about my learning preferences, challenges, and goals

    * Step 2: AI generates a “language DNA profile”

    * Step 3: I record myself speaking the language for five to 10 minutes → upload the transcript + my DNA profile → AI gives feedback tailored to me

    This is a workflow rather than a full automation because I still trigger each step. I generate a profile. I upload the inputs. I hit go.

    Here’s how to build your own AI workflow:

    * Pick one task you do repeatedly and turn it into a 3-step workflow

    * Pick one or two tools to help you optimize this workflow

    * Write a prompt for each step. If possible, add examples of what “good” looks like.

    * Test it with a real example and iterate until the output is what you need

    * Set up a Project (in ChatGPT or Claude) to keep your context, instructions, and reference files in one place

    Resources for this stage:

    * Claude Cowork for beginners

    * Claude in Chrome

    * Claude Skills: part 1, part 2

    * Before you use Cowork, create this file

    For most professionals, this stage is more than enough. But if you want to multiply your output without working more hours, there’s one more level.

    Stage 5: AI System Builder

    Stage 4 was about workflows you run. Stage 5 is about systems that run themselves.

    There’s a mindset shift here.

    You stop asking, “How do I do this faster?” Instead, you frame the question as, “How do I build something that does this for me, even when I’m sleeping?”

    Here’s a system I recently built:

    The problem: I publish daily Substack notes. Many of my notes are inspired by viral content I find on Instagram, YouTube, and X. The old process took hours every day: saving links, watching videos, downloading images, writing hooks, etc.

    The system I built (simplified):

    * Collection: My team and I save viral content to a shared group chat throughout the day

    * Trigger: At 3 a.m., an automation kicks in (I’m sleeping)

    * Processing: Claude reads the group chat, checks what’s new for today, then downloads everything (text, images, videos)

    * Generation: Each piece runs through my Substack notes generator (a separate workflow that uses my brand voice and note formats)

    * Output: When I wake up, I open my “Today” folder. Inside are 3 subfolders: YouTube, X, and Instagram. Each has media content + 5 draft notes ready to edit and post.

    I pick one draft, edit it, and post it. What used to take two to three hours now takes minutes.

    To build AI systems, you need tools that go beyond chatbots:

    * Claude Cowork: My favorite for delegating things to Claude without being technical. It runs in a sandboxed environment for safety, so you may run into limitations.

    * Claude Code: A more advanced version of Cowork. I use it whenever Cowork can’t build something for me. You don’t need to be a coder. You describe what you want, and it builds it. Caveat: it can feel scary at first.

    * n8n: Popular no-code tool for AI agents and multi-step systems. I don’t use it, but many builders do.

    Resources for this stage:

    * How to set up Claude Cowork

    * How and why to set up scheduled tasks

    * Google Doc list of AI guides

    Two Final Tips

    * Don’t skip stages. AI literacy and prompting may feel boring compared with building your own app, but they make every stage above them work better.

    * You don’t need to be at Stage 5 to get serious value. Many professionals get a 2x improvement just from reaching Stage 3.

    Pick one stage above where you are right now and focus on it for the next few weeks. That’s how you’ll go from AI beginner to pro by the end of 2026.

    Thanks to Frank Andrade for this guest post.



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    7 min
  • My 20 Favorite Google Docs Features ❤️

    Google Docs turned 20 this year, so I’m sharing 20 of my favorite GDocs features you might find useful. What are your favorites?✨

    1. Type with my voice 🎙️

    Tools > Voice typing

    When I’m tired of typing, I dictate. I like voice typing with Google Docs to add sentences to a blank page as I think out loud. Here’s a sample of my dictated text. Read it aloud to test your voice typing. The transcription isn’t perfect, but it’s free.

    2. Match a prior doc’s format 📋

    File > New > Help me create > Match doc format

    I can base any new doc on a prior design, like my pedagogy resources handout. This gives me a quick way to create new styled drafts. Requires Gemini to be turned on.

    3. Add extensions 🧩

    Extensions > Add-ons

    Get apps for GDocs. I like Beep for attaching voice notes to docs. Word Cloud Generator is nice too. Here’s an example, drawn from this post. Docs to Slides by Alice Keeler is useful for converting a doc into a presentation. The Free icons extension from icons8 is useful for easily adding little visuals to a doc.

    4. Add a quick link to any text 🔗

    Type Command+K with any word or phrase selected

    Google Docs is the most efficient tool for adding links to text. Select a word and press Command+K to choose from several relevant links without leaving the doc. It helps me avoid opening a separate tab to hunt down links. Here’s a gif showing this.

    5. Quickly create a new doc ⚡

    Type doc.new into any browser to quickly create a document.

    This shortcut lets you jump into a new document from any browser window. It works with other Google services too: slide.new, sheet.new, form.new, site.new, cal.new, meet.new, and keep.new. It also works for notion.new, canva.new, substack.new, and playlist.new (Spotify). More examples.

    6. Divide a doc into sections 🗂️

    Insert > Tab

    Instead of creating 20 files for a project, make a single doc your headquarters. Each topic can have its own tab. Or each team can. Share everything with one link instead of maintaining a dozen separate docs. See my tips for tabs then add your own idea in a comment. (View a published GDoc version to see the difference between shared docs and published ones).

    7. Add a table of contents 🧭

    Insert > Table of contents

    For long documents, create a table of contents (TOC) so people can quickly find what they need. Choose the black text option for a cleaner look, if you’re printing.Add headings within the doc (Format > Paragraph styles) to ensure they appear in the TOC. Here’s step-by-step help on this if you need it.

    8. Keep track of changes 🕰️

    File > Version history

    Version history makes it easy to see what you’ve changed, when. Or look at what collaborators have edited. See what’s new, who made an edit, and when.

    9. Copy a doc 📑

    File > Make a copy

    Duplicate something to make a different version. Simple, easy, and fast. Sometimes I use this for version control instead of the built-in version history.

    10. Download a PDF — or other formats ⬇️

    File > Download > PDF Document

    Sometimes I need to share a PDF so anyone can easily read my doc. Nothing fancy, but it’s been useful hundreds of times.

    11. Create typing shortcuts ⌨️

    Tools > preferences, then select Substitutions on the top right.

    Use shorthand with GDocs for words or phrases you frequently type. List them in your preferences. For each one, pick a simple key combination of letters. From then on, any time you type those letters, they’ll expand into your desired phrase. It’s useful for your email or mailing address, or a word you often misspell.

    12. Try new templates 🎨

    File > New > From a Template

    Start from a design instead of a blank page. Google now has more than 100 templates, including 60 in the template gallery and 40 when you choose the “from a template option” to start a new doc. The new project roadmap and onboarding templates are well-designed. The resume, letter, and proposal templates also make your words look good. Some of the other templates are a bit visually bland.

    13. Design docs for the web 🖥️

    Format > Switch to Pageless

    Many of the docs we create never need to be printed. So GDocs now offers a pageless format for docs you’ll use on screen. It lets you include wider images and eliminates artificial page breaks. See a gif of Pageless view. Here are a few more points about this format.

    14. Listen to your words 🎧

    Insert > Audio Buttons

    When I hear my writing read aloud, the clunky bits jump out. That helps with editing. When an AI voice reads my writing, I can look away and devote my full attention to listening. This feature lets you choose from seven synthetics voices. They don’t sound like robots. This feature requires an AI subscription or an eligible Google Workspace plan.

    15. Get proofreading help 🔍

    Tools > Proofread

    Check for spelling or grammar errors. Get suggestions for where you might break up overly long sentences or avoid passive verbs. You accept or reject changes one by one. I like getting to decide which fixes make sense. It’s like an augmented spellcheck that requires AI settings to be turned on. See it in action on a prior draft of this post.

    16. Translate your doc instantly 🌍

    Tools > Translate document

    Share your doc in another language. GDocs keeps your original and makes a translated copy. It’s not human quality, but it’s enough for the gist.

    17. Use markdown for formatting #️⃣

    Enable it under Tools > Preferences

    Easily add headings, bullets, and other formatting from the keyboard with simple symbols. Use *ital* for italics or **bold** to make something bold. You can also paste markdown text from other apps with Edit > Paste from Markdown

    18. See who’s viewing your doc 📊

    Tools > Activity Dashboard

    A dashboard you may not have noticed shows who else in your organization has viewed a doc and when. You’ll also see a chart showing when comments have been added. It requires Google Workspace, and it’s not available for solo free accounts. Adjust privacy settings to keep your activity secret.

    19. Insert interactive elements 🧱

    Insert > Building Blocks

    Include an AI summary of your document, a decision log, a team directory, a content tracker, or other templated, editable text blocks. Or insert a linked doc that updates automatically when you update the original file.

    20. Link to people, events and docs with Smart Chips 🏷️

    Insert > Smart chips

    Smart chips let you paste a live link into docs with a preview. Type @ and the name of a person, place, or calendar event to insert a preview that pops up when someone scrolls over the item. See Google’s help explanation.

    Bonus tip: Add more fonts 🔠

    Fonts > More fonts

    Georgia, Raleway, Proxima Nova and Oswald look good. And they’re easy to read. But experiment with other new fonts. Use WhatTheFont to identify other fonts you see and like online.

    5 ways GDocs disrupted word processing 🚀

    Free. Make and store thousands of documents at no cost, with no ads.

    Auto-Save. Write without fear of losing files. Work is auto-saved constantly. I remember the frustration of losing docs when Microsoft’s old Word crashed.

    Accessible. Get access to your documents on any device. No need to carry disks around or have a specific device to access important files.

    Collaboration. Share docs with others, or publish them. I’ve used docs to liveblog, to share examples publicly. Or work privately.

    Simplicity. Just start writing. No complicated menus. It just works reliably.

    See more Wonder Tools posts about Google Docs 🪎

    Good alternatives to Google Docs 🔄

    * Kraa is a slick text editor I like. Create simple, polished pages like this gallery, library, or archaeology article. It has new sharing features. The iOS app is coming soon.

    * iA Writer offers a simple, minimalist writing view.

    * Versey is a promising new option I’m testing, with AI to help with editing. Textjam and Reproof are others I’m trying, though not yet recommending.

    * Superhuman Docs, formerly called Coda, is underrated. It’s an alternative to Notion that lets you incorporate AI in your workspace and connect documents to your calendar, CRM, email, and Slack.

    * Craft remains one of my favorite



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    12 min
  • Your AI Teaching Toolkit 🍎

    I’m excited to be starting a new semester this week, like millions of other teachers. As a resource for my fellow educators, I’m updating a piece I wrote for The 74, the nonprofit education news site.

    The average K-12 teacher works 49 hours a week. About a quarter of that time is uncompensated. In higher ed, adjuncts make up about 40% of the faculty workforce. At many institutions, time spent on course prep and administrative tasks is unpaid. Most teachers I know didn’t become educators to spend evenings generating quiz questions, rewriting instructions, or filling out administrative paperwork.

    AI assistants like Claude, ChatGPT and Gemini won’t change these realities. But when you’re overwhelmed, they can help streamline tedious tasks. They can free up energy for what only a human teacher can do. When used thoughtfully, these tools can actually push us to be more creative. They can help us overcome teaching ruts, nudging us to revitalize how we show up in the classroom.

    A 60-second guide to prompting

    The first step to making the most of AI is understanding how to use prompts. A prompt is a natural-language instruction to an AI assistant. It doesn’t have to include technical or formal language. You don’t even have to use full sentences.

    Prompts work with any AI assistant. Use free private AI chatbots, like Proton’s Lumo or Duck AI. Or download AI apps that run on your laptop without touching the Internet, like Jan, which I tested and recommend. Claude, Gemini, and ChatGPT also work well. Whatever you have access to will work.

    As the teacher, you guide an AI assistant with relevant context. Prompts work best when they include specifics. Generic prompts yield generic responses.

    It helps to iterate on AI output with follow-up prompts. Ask for more specificity or detail. Adapt the response for your students. Don’t use it as is. Part of retaining your agency in the process is making sure you build on whatever outputs an assistant generates. You’re the director. It’s much like adopting an open educational resource. The advantage, though, is that this material will be more tailored to your students and teaching approach.

    Knowing how to use prompts effectively can mean the difference between AI that’s actually helpful and AI that’s gimmicky. The prompts below offer a creative boost. Each illustrates a practical way to use AI in support of thoughtful, pedagogically sound teaching. You don’t need any special technical skills. You don’t need paid AI subscriptions. Customize them to suit your subject matter and your approach to teaching.

    Try my new free Teaching Prompt Assistant. Give it your goal and it’ll guide you quickly to a draft prompt.

    Start with a project

    If you want to use prompts more efficiently, first create a project in Claude or ChatGPT, or a Gemini Notebook. Think of this as a folder where you provide context about your class that an AI assistant can reference when you ask for support. You can upload past materials, syllabi, lesson plans, curriculum guidelines, Common Core State Standards, or whatever else is relevant for your teaching.

    You can also add detailed instructions to the project explaining how you’d like the AI to assist you. You’re teaching it your preferences. Once you set up a project, you won’t have to repeatedly type in the same context.

    The Prompt Collection

    1. The Bell Ringer

    Start class with a spark

    The first five minutes of class set the tone for everything that follows. A short, well-designed opening activity can draw students in. Engaging openers are especially valuable on Mondays, after vacations, or when you’re pivoting to a new topic. The challenge is coming up with fresh ones regularly.

    Goal: Generate five quick options for activities you can use at the start of a class session, adapted for your subject and your students.

    Prompt: “I teach [subject x] to students in [grade level x]. We’re studying [specific topic xyz]. Generate five activities I can adapt to start a [xx] minute class. Each should take no more than [x] minutes, require no materials, and either activate prior knowledge or help students reflect on what they’ve just learned. Include one that’s discussion-based, one that’s written and one that’s a game or visual/creative task. [Or adapt these examples to reflect your subject matter. For example, one of the options could be a logic puzzle or an artistic challenge].”

    Tip: Be as detailed as possible about your preferences. Include a sentence about your teaching style and context about your students. No need to make it formal.

    See an example of a Bell Ringer Prompt

    2. The Real-World Hook

    Answer “Why does this matter?” before students even ask

    When you’re overwhelmed by administrative meetings, multiple preps, and paperwork, it can be hard to give extra attention to helping students relate to a new unit. This prompt helps you brainstorm connections to contemporary music, art, film, TV, cultural trends or other subjects of interest to students.

    Goal: Generate five ways to show your students how the topic you’re teaching is relevant to their lives, each with a two-sentence hook you can use to open discussion.

    Prompt: “I’m about to begin a unit on [x topic] with [grade level x] students. [Provide a sentence of additional context and a few additional details about your students’ interests]. Generate five ways to connect this material to something students are likely to relate to. This can include sports, the arts, social media trends, pop culture, music or other contemporary issues. For each connection, suggest a two-sentence hook I can adapt to help jumpstart a class discussion.”

    See an example of a Real-World Hook Prompt

    3. The Bad Example Generator

    Turn common mistakes into learning opportunities

    Showing students examples of mistakes can help them avoid those pitfalls. But you can’t embarrass students by showing examples of their weakest work. Fortunately, AI assistants are excellent example generators. They can come up with nearly any kind of error you specify. No need to spend hours creating intentionally bad work.

    Adapt this prompt to include any kind of error you want your students to avoid. These can include experimental design mishaps in science or mangled math formulas. If you’re teaching essay writing, showcase logical fallacies or ad hominem arguments.

    Here’s an example of a table of common writing traps I generated.

    Goal: Produce five realistic examples of a specific error type, unlabeled, so students can identify, discuss and learn from the flaws.

    Prompt: “I’m teaching [x subject/topic] to [grade level x] students. [Provide an additional sentence of specific context about your class, the learning goals you’re focusing on, and/or the lesson you’re preparing.] Generate five examples of paragraphs with [ad hominem arguments / circular reasoning / weak thesis statements / misleading use of statistics / or pick any other weakness] related to [x topic]. Make sure each example is realistic. These should be the kinds of errors students at this grade level might actually make. Don’t label what’s wrong. I’ll use these for a class activity where students identify and explain the flaws themselves.”

    Tip: You can also task the AI with annotating or explaining these errors to help you walk students methodically through these common flaws.

    * See how a specific teacher might use the Bad Example Generator

    * Try my free “Wrong On Purpose” tool to generate examples of what to avoid that you can tailor for your class. (Requires a free Claude account)

    4. The Scaffolding Prompt

    Make instructions clear for every student

    Complex instructions often trip up students. Simplifying language can help, along with breaking guidance into smaller steps. This prompt helps you clarify instructions for an existing assignment, handout, or any other activity. It’s particularly useful if you have students with learning differences or if your class has a wide range of readiness levels.

    Goal: Reframe a handout or assignment so it’s clearer and more accessible, especially for stu…



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    17 min
  • 🤔 Odd Tools That Are Actually Useful

    I’ve always admired the way bestselling author A.J. Jacobs turns his life into a laboratory for testing quirky ideas. He’s written books about following every biblical law for a year, reading each entry in the encyclopedia, and thanking a thousand people responsible for his morning coffee. I consider it immersion journalism. He calls himself a human guinea pig.

    So I was delighted to meet A.J. at a recent Substack event. Afterwards we spent an hour talking live on Substack about two dozen of the odd and creative tools he uses and trading ideas about our experiments. Watch the recording above, including some surprising confessions, and see a summary of the tools and links mentioned below.

    Add surprise to your day

    Algorithms narrow what we see and filter outliers. So A.J. seeks out serendipity.

    * Wiki Roulette serves up random Wikipedia entries, while Window Swap lets him peer out of windows all over the world.

    * Ground News A.J. uses this app to see how outlets across the political spectrum cover the same story. Its Blindspot feature surfaces stories covered mostly by one side. I mentioned a related newsletter, The Flip Side, which picks a daily topic and spotlights commentary from the left and right.

    * Seek out surprises A.J. asked Claude for 10 articles he would probably find boring, annoying, or offensive. It surfaced one gem, about ancient Egyptians buried with golden tongues so they could speak in the afterlife.

    * Try it yourself Here’s my own anti filter-bubble prompt, and the 5 odd links ChatGPT gave me in my first experiment.

    * Serendipitous Reddit For stumbling onto curiosities, I’ll type a keyword into the Reddit search box. During my live chat with A.J. I found r/Whatisit, where people post photos of unidentifiable objects. The crowd figures out what they are. And r/MadeMeSmile, which is heartwarming. Try the free Random Reddit Stumbler Chrome extension to discover new Reddit communities. Caveat: You might waste time procrasti-surfing in rabbit holes.

    * A.J.’s NYTimes archive trick Search the Times all the way back to 1851 for a word of your choice, then read early mentions. Searching for “dogs” led A.J. to a disturbing 1896 editorial titled “All Dogs Deserve Death” (screenshot), which argued that dogs spread disease. “It was proof that clickbait is not a totally new phenomenon,” he says. A.J.’s caveat: the archive surfaces ugly history. Searching “cocaine” turned up overtly racist reporting. Accessing the archive requires a subscription.

    * Read A.J.’s take on injecting randomness into your life

    Play with words

    * Parseword The creator of Wordle, Josh Wardle, made this tricky new word game. A.J. describes it as an on-ramp to British cryptic crosswords, which blend wordplay with anagrams and obscure puns. “They’re infuriating,” he says, “but at the same time, very addictive.” I find this one fun but hard.

    * Raddle Try this word ladder with a twist. The clues are are out of order. A.J. says he enjoys it because you can finish in two minutes. I appreciate the hints so I don’t get stuck.

    * OneLook “An amazing search engine for words,” A.J. says. Type a word and get its history, related terms, definitions from numerous dictionaries, or quotes, phrases, and lyrics that use it. Or use wildcards to find words that start or end with a group of letters. OneLook scans 17 million entries in 805 dictionaries to answer queries. They also designed an amusing new word game called Cadgy.

    * Anagram sites. The Word Finder and other multi-word anagram tools like Anagram Solver handle phrases, not just single words. Scrabble Solver helps you find words with your tiles.

    * Droodles This playful format for minimalist drawings centers on absurd captions, as in these examples. Play by guessing the captions, or make up your own.

    Wake up your senses

    * The Sommelier Wine Aroma Kit by Aromaster A.J. bought is a training kit for aspiring oenophiles. It has 88 tiny bottles of individual scents, including Rose and Lemon. Horse sweat, the set’s last bottle, isn’t something you want in a wine. The kit is $400 on Amazon, but you can make a simpler one for $30. A.J. tries to identify scents for three minutes each morning to strengthen his nose for food. Smell is our least trained sense, he says.

    * Use your own spice rack When my daughters were little, we’d play a guessing game, taking turns holding a spice bottle beneath our noses with our eyes closed. It entertained us in the kitchen and cost nothing.

    * Vision-distorting glasses A.J. ordered 10 pairs that alter how you see. One simulates a bee’s vision. Another tries to represent macular degeneration. Some are prisms that flip the world upside down. He started this exploration after hearing that yellow-tinted glasses brighten your mood. The tint did little for him. But it made a point, he says. “What we see is a very narrow spectrum of reality.”

    Watch movies better

    * Audio description Most streaming apps have an accessibility feature that lets you hear a narrator describe what’s happening on screen. It’s designed for blind and low-vision viewers. A.J. isn’t vision impaired, but uses it anyway. “It’s educational,” he says. “I learn a lot from the voiceover that I didn’t know before.” Watching an Agatha Christie film, he discovered what a cloche is. And a trilby. The narration also alerted him to a novel detail: the O in the Focus Features logo is deliberately out of focus. A.J. says he admires the concise writing required to fit every word between the dialogue.

    * Closed captions A simpler feature we both use. A.J. turns them on for song titles and for accents. “You’re watching Derry Girls and you have no idea what people are saying.” I started relying on captions for The Wire.

    * Playback speed A.J. watches films at 1.5x or 2x speed. “I see twice as many movies,” he says. “I admit, I may get 80% as much out of them.” He knows filmmakers hate it.

    * Netflix offers 1.5x, but not while casting or on the ad-supported web player

    * Apple TV and Prime go to 2x

    * Chrome extensions like Video Speed Controller give you finer control

    * Slow motion A.J. also watches at 0.5x speed sometimes to study scene design. Dense shows like Veep need to be slowed down, he says, not sped up.

    * WhenJumpScare A.J. appreciates psychological horror, but he hates jump scares. This free site tells you exactly when surprises are coming so you can look away. “I love a horror movie,” he says, “and I’m not going to watch it if I’m going to be jumping in my seat the whole time.”

    * RunPee (iPhone/Android) This free app (screenshot) tells you the ideal minute to run to the bathroom during a long movie, and sums up what you missed. A.J. used it for Christopher Nolan’s nearly three-hour Odyssey.

    Stretch your brain

    reMarkable tablet We both own one. I use mine to sync, back up, and organize my handwritten notes. A.J. never connects his to the internet. Every morning he spends ten minutes brainstorming with it by hand.

    Sometimes he flips open a magazine for an improvised prompt. He saw a snowman picture recently and started riffing: “What if it’s a snow woman? What if the pipe is a vape? What if the coal eyes are solar panels?”

    “99% of these ideas are terrible,” he says. But he doesn’t mind. “If you believe the brain is a muscle, and I do believe there’s something to that metaphor, then this is like going to the gym for me.”

    Add color to your space

    I shared with A.J. three of the most colorful objects in my office. I have no affiliation with any of these companies. I’m just sharing what’s on my desk.

    CMY Cubes A small glass cube reflects light next to my laptop. Each face has a different color. Look through it at an angle and the light refracts into new colors. Designed in Australia, the smallest cubes cost about $23. No batteries, no app. I found mine at the Toy Fair, the annual trade show at NYC’s Javits Center where thousands of toymakers show new wares.

    Merge Cube A foam cube that supplements augmented reality apps. When you…



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    1 hr 3 min
  • Connect Your Tools to AI 🔗

    I’ve changed how I use Claude and ChatGPT lately. They’ve become my digital dashboards, linked to many of the tools I rely on.

    I can ask Claude to add to my calendar, query my meeting notes, update me on my email, or find a passage I highlighted in my digital notebook.

    Claude Connectors and ChatGPT plugins connect to hundreds of services. These include Superhuman Mail for email, Google Calendar, Granola for meeting notes, and Readwise for my online highlights.

    Read on for how and why to link your favorite tools to your AI assistant, and examples of connections and queries I’ve found useful so far.

    Bonus: I made this new online guide for you based on this post as an experiment with ChatGPT’s new Sites feature. I also made a tipsheet with Claude artifacts to help you get started.

    Why Connecting Tools to Claude and ChatGPT Is So Useful

    Claude and ChatGPT know the context for my work because I’ve set up Projects for my primary work areas. Each has detailed instructions and reference documents. And the AI has a memory of the work I do, my style, my preferences, and my objectives. So I can ask my AI assistant to:

    * Plan: Add four prep sessions to open morning slots on my calendar next week for the classes I’m teaching this fall. Include in each event description relevant excerpts from my meeting summary and reference the recent planning notes I dictated.

    * Research: Gather recent links I’ve saved to Raindrop, my bookmarking tool, that might be relevant to my team’s research. Then create a new reminder with those links and a summary of my recent related notes.

    These multiple-part commands require context. They won’t work in Google Calendar, Raindrop, or Granola directly. That’s why it’s so helpful to have Claude or ChatGPT as the command center.

    Sponsored Message

    Remember More of What You Read

    I often finish a good nonfiction book with a handful of useful ideas. Then I gradually forget the details. Can you relate?

    Shortform gives me a practical way to revisit the books I want to remember. Its guides are written and edited by people, not robots. The guides include clear book overviews as well as deeper analysis, which I appreciate because I want to get beyond the surface. I also like that the guides include examples and quotes. And they often mention connections to related books, which is useful for ideas on what else to read.

    On the Shortform app I recently read the guide to The Meaning of Your Life, by Arthur Brooks, which led me to Vivek Murthy’s book, Together, about the loneliness epidemic.

    I use Shortform both to refresh my memory on books I’ve already read, and to explore potential new titles before I decide what to read next. Try it to find guides for business books, education, psychology, biography, and more.

    Wonder Tools readers get a free trial and $50 off the annual plan.

    MCP is the New USB 🔗

    These connectors have a technical name: MCP, or Model Context Protocol. But just as you don’t need to think about USB details when you plug in a printer, or http specifications when you use the Web, you can use MCP without understanding its technical details. All you need to know is that MCP is a way of linking software tools, sites, and apps to AI platforms like Claude and ChatGPT.

    Remember the world prior to USB? Printers, hard drives, cameras, and external monitors had their own special cords to connect to your computer. I just cleaned out dozens of them from a drawer in my Manhattan apartment. Now they’re obsolete because USB ports are everywhere. MCP is a similar unifying standard for linking tools to AI.

    5 Ways I’m Using Tools Connected to Claude

    Manage Email 📧

    I rely on Superhuman Mail to read, organize, and respond to email. It’s fast, easy to use, reliable, and integrates with my calendar. I use it with three distinct email addresses. Because I have to act on important messages, I’ve linked it to Claude.

    Get started: The connection guide walks you through linking your email to Claude or ChatGPT. You can then ask your AI assistant to:

    * “Help me turn a bunch of starred emails into an afternoon plan.”

    * “List important messages I’ve sent this month that the recipient hasn’t yet opened.”

    * “Draft concise responses to routine customer questions for my review.”

    Some of these tactics will also work with Gmail and Outlook connectors.

    Example query: “Look at my five most recent starred emails, suggest an action list for this afternoon based on my priority list, then put an hour on my Google Calendar to act on them.”

    Do More with Meeting Notes 🗒️

    I use Granola as my notepad during meetings. It transcribes conversations, then creates a summary based on the transcript and my own notes. (See my guide). I can already ask questions about my meetings in Granola without needing a separate AI tool.

    But the advantage of linking Granola with Claude (or ChatGPT) is that Claude has access to insights in my notes, email, and Google Drive, so it can integrate the info it pulls from Granola within the context of a broader analysis.

    Get started: The Granola MCP guide explains how to link it to your AI. Unlike many other paid services, Granola actually lets free users query meeting notes (for the past 30 days) using your AI tool of choice.

    Example query: “Give me a summary of the research questions I said I’d follow up on in my meeting with Pat. Next to each task include a bulleted list of the background details I already collected in my research spreadsheet.”

    Edit Images and Videos 🌆

    Photoshop and Premiere are powerful but complicated. Now you can edit an image or video without even opening a separate app. Set up the plugin, then tell your AI assistant to use it in your prompt. The AI assistants are often clever enough to figure out which tool to use even if you don’t explicitly mention it.

    Get started: Install the Adobe app in ChatGPT. Or add it to Claude, using this guide. Your AI assistant will now have access to the capabilities of Photoshop, Premiere, Firefly, Express, Acrobat, and other Adobe apps. You don’t even need an Adobe account to get started, though it might be helpful to get a free one if you want to organize, improve, and act on your creations later. (Canva’s MCP is also useful).

    Example query: “Help me change the text in this graphic.” Or “Reformat this horizontal video clip for YouTube Shorts or Instagram Reels.” Or “Add background blur to this headshot, fix the lighting, and crop it for a portrait.”

    As a test, I changed the first line in an illustration from “Bold” to “Kind.” Notice that the first attempt wasn’t perfect. The period after “Kind” was missing. But a quick edit request fixed that. The Photoshop edit preserved the font, style, spacing, and angle.

    The benefit: Instead of hunting through Photoshop menus trying to figure out how to do this, I just asked ChatGPT to use Photoshop to make a change. In the long run, being able to use natural language to accomplish tasks like this may shift how we spend our time away from technical menu-hopping toward more creative work. We’ll spend more time thinking about what to do and why, rather than how to technically get it done.

    Find Highlights 📚

    I use Readwise to collect the passages I highlight when reading online or on my Kindle. It also hosts passages I save when listening to podcasts with the Snipd app.

    Get started: The Readwise MCP lets you make use of the highlights you’ve made while working on other projects with an AI assistant.

    Example query: “Show me a bunch of my Readwise highlights that include descriptions of desserts, especially from European novels, then gather a list of related recipes I can make with my daughters before our trip.”

    Research Legal Cases 🔎

    Court Listener from the Free Law Project is a handy way of gathering info about court cases. You can ask for records related to Elon Musk’s recent testimony without paying for a legal rese…



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    10 min
  • 📍 Pinpoint, Explained

    Google’s Pinpoint is now open to everyone. It’s a surprisingly powerful free tool for making sense of giant piles of digital stuff. (Before June 3, it was restricted to journalists and academics). Read on to learn more about creative ways to use Pinpoint; its new AI features and their limitations; and how Pinpoint differs from NotebookLM.

    How Pinpoint Works

    Pinpoint lets you store and analyze hundreds of thousands of files so you can find tiny needles in gigantic digital haystacks.

    * Pinpoint can transcribe hundreds of hours of audio and video.

    * It also makes your handwritten text, scans, and PDFs searchable, like my enormous collection of scanned handwritten notes and whiteboards.

    * Once Pinpoint processes your files you can search, summarize, and organize your collections.

    * Pinpoint makes it easy to query, label, and extract data from hundreds or thousands of documents. It’s simple to use. No complex menus or commands.

    Getting Started

    * Start by uploading PDFs, emails, audio and video files, handwritten notes, or other file types.

    * Each collection can have up to 200,000 files. You can have an unlimited number of collections, which function like folders.

    * Journalists and academics can request “Pinpoint for Professionals,” which provides 100GB of storage. Others start with 1GB.

    * Audio and video files can be up to 2 hours long and 8GB. The limits are much more generous than what other AI tools, like NotebookLM, offer.

    * Pro tip: Create separate Pinpoint accounts for each of your Google accounts. That gives you more storage. It’s also how I keep personal projects separate from work. You can always download files you’ve previously uploaded. And request additional storage if you reach your limit.

    Pinpoint Features to Try

    * Scour through audio recordings to locate key moments. Pinpoint transcribes in more than 100 languages. Upload and transcribe your recorded presentations to review how you frame a particular topic. Or how water pollution is described in local council meetings.

    * Explore text within images and handwritten notes. I’ve scrutinized my old handwritten notes for ideas and checked whiteboard photos for explanations I can improve.

    * Share a document collection. Invite individual collaborators or publish a collection for public exploration. Giving readers access to source material can be a valuable form of transparency in journalism.

    * Analyze an email or document archive. Assess a public email trove or document collection, like files from the Enron trial, for connections between politicians and companies, or financial impropriety.

    * Focus your research on particular people, organizations, locations, or date ranges. Pinpoint automatically lists a collection’s most frequently-mentioned entities. Click on an entity to jump to exactly where it’s mentioned.

    * Export important Gmail folders with Google Takeout in .mbox format. Takeout lets you export and back up anything Google hosts. You can then upload your email collection to Pinpoint to find patterns, or locate references to specific people, places, or organizations.

    🎁 Try my new Pinpoint Assistant to get personalized ideas for how you can use Pinpoint for a project you’re working on.

    Pinpoint in Newsrooms

    News organizations have relied on Pinpoint for award-winning investigations involving thousands of documents, including:

    * Blind Spot by the Boston Globe (Pulitzer)

    * Poisoned by the Tampa Bay Times (Pulitzer)

    * Secret Sauce: Expired from North Carolina’s Blue Ridge Public Radio (BPR) (Edward R. Murrow Award).

    * Z. Waite’s detailed case study explains how and why BPR used Pinpoint. Waite also notes four good, free, alternative tools: DocumentCloud, Datashare, OpenRefine, and Datasette.

    Public Collections

    * Pinpoint’s “Explore” section lets you examine document collections from more than 200 news organizations, ranging from The New York Times and The Washington Post to The Hindu and Süddeutsche Zeitung. Test out the searching and filtering features before uploading anything.

    * Notable document sets include JFK assassination records, Mueller Court filings, and 80 years of U.S. foreign agent registrations (86,018 documents) uploaded by the Center for Public Integrity.

    New AI Capabilities

    Pinpoint has a bunch of new AI features in beta available in more than 80 countries. In my testing, not all of the AI capabilities work reliably yet, but you can request early access. Pinpoint’s AI features are designed to help you analyze your files, not generate original content as you might with Gemini or NotebookLM.

    * Explain words or phrases in any file. Highlight any text and ask Pinpoint to put it in context. I like the short, useful explanations based on what else is in a document.

    * Google words or phrases inside your text to learn more from Google. In my tests, this beta feature consistently yields error messages.

    * Summarize Collections. I like how Pinpoint gives me an AI-generated overview of every file I upload. It can also summarize an entire collection.

    * Extract data into spreadsheets. Pull info from up to 100 documents at once and deliver it as a sheet, with links back to the source text for each data point. That’s handy for tracking mentions or doing comparative research. Try this feature for analyzing public government contracts or other information in PDF form that would be easier to work with in a spreadsheet.

    * Automatically label hundreds of your files in a collection. Let’s say you have a public email dataset. You may want to evaluate just those written by a particular person, or just those discussing a particular stock. Instruct Pinpoint and it will label your collection for you. Limitation: Pinpoint can label 1,000 files at a time. In my tests, the interface only let me select 100 files. If you’re working with tens of thousands of files, labeling may be tedious.

    * Transcribe audio quickly. Pinpoint now claims to give you high-quality transcribed text 20x faster than it used to. I couldn’t verify that specific metric, but it’s generally fast. Each file is helpfully time-coded. Click on any section of text to hear the corresponding audio. Limitation: unlike Wispr Flow and Letterly, which I use for my personal dictation, Pinpoint sometimes mangles names, and doesn’t learn from its errors.

    * Compare any two or three files. See what changed in multiple versions of a document, or how three different people addressed the same subject.

    * Query your collection with ordinary language. Results are often fast, useful, and linked back to the original document. Expect occasional errors, though. One search I tried, for example, returned a document mentioning someone with a similar but different name from the one I was searching for.

    * Create a timeline. If you’re looking at how something developed over time, you can pick up to 100 files and generate a timeline. You can optionally specify a topic for the timeline. This might be useful if your dataset has dated transactions, for example, or multiple reports you want to put in order.

    Pinpoint vs NotebookLM

    * What’s similar: Both NotebookLM and Pinpoint are free Google services that allow you to efficiently summarize and search though large documents.

    * What’s different: NotebookLM synthesizes and generates (slides, infographics, video and audio podcasts, and reports). Pinpoint, on the other hand, focuses on finding patterns and organizing a wider array of file types in much larger collections of email, multimedia, and scanned images.

    * NotebookLM allows 50 files per notebook for free users. (See my guide). Pinpoint lets you upload 200,000 files into each collection.

    * Combine the two: If you have a large collection of documents, consider gathering, storing, organizing, and transcribing in Pinpoint. Then move the most important files into NotebookLM for further analysis and to generate artifacts like reports, slides, infographics, flashcards, audio, and video.

    Privacy

    * Your documents …



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    8 min

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Wonder Tools helps you discover the most useful sites and apps. Building on one of Substack's most popular productivity newsletters, each episode of the podcast includes specific tips on how to make…